m-Chloroperbenzoic acid → 3-Bromo-2-chloro-6-methylpyridin-1-ium-1-olate

HRID 559139

반응식

HRID 559139 반응식
[Br:1][C:2]1[C:3]([Cl:9])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:18])C=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([Cl:9])=[N+:4]([O-:18])[C:5]([CH3:8])=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 27344183-Bromo-2-chloro-6-methylpyridine

생성물 1

HCID 857064893-Bromo-2-chloro-6-methylpyridin-1-ium-1-olate수율 1,230.1%

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
50 °C

실험 절차

step a—To a solution of 3-bromo-2-chloro-6-methyl-pyridine (2.0 g, 0.687 mmol) in CHCl3 was added MCPBA (3.3 g, 19.1 mmol) and the resulting solution was heated at 50° C. overnight, The resulted solution was cooled and partitioned between DCM and sat'd. aq. NaHCO3. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (30 to 80% EtOAc) to afford 1.88 g (87%) of 3-bromo-2-chloro-6-methyl-pyridine 1-oxide (52a) as a white solid.

후처리

  1. temperatureThe resulted solution was cooled
  2. custompartitioned between DCM
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by SiO2 chromatography
  7. washeluting with an EtOAc/hexane gradient (30 to 80% EtOAc)

출처 및 근거

ORD 기록
ord-9a9ed184c34a4dcab8378a41dd3dc6e1
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063072B2

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